


Cheering up Bill

by ML55555



Category: IT (Movies - Muschietti), IT - Stephen King
Genre: Anal Fingering, Anal Sex, Blow Jobs, Double Anal Penetration, Double Penetration, First Time, M/M, Overstimulation, Triple Penetration
Language: English
Status: Completed
Published: 2020-06-28
Updated: 2020-06-28
Packaged: 2021-03-04 07:02:54
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,791
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24965662
Author URL: https://archiveofourown.org/users/ML55555/pseuds/ML55555
Summary: Eddie, Stan, and Richie have a plan to make Bill feel better after Georgie's disappearance.
Relationships: Bill Denbrough/Eddie Kaspbrak, Bill Denbrough/Eddie Kaspbrak/Richie Tozier, Bill Denbrough/Eddie Kaspbrak/Richie Tozier/Stanley Uris, Bill Denbrough/Richie Tozier, Bill Denbrough/Stanley Uris, Eddie Kaspbrak/Richie Tozier, Eddie Kaspbrak/Stanley Uris, Richie Tozier/Stanley Uris
Comments: 1
Kudos: 69





	Cheering up Bill

To his few friends, Eddie, Richie, and Stan, it was obvious that Bill was not okay, he hadn’t been ever since his brother disappeared one day. They all tried to help him search for him, but it was obvious they weren’t going to find him, but Bill kept insisting they search so they did, not wanting to let down their friend, and leader. Tonight they were going to have a sleepover at Stan’s house since his parents were out on some trip and they had a plan to cheer him up, hopefully. 

The first to arrive at Stan’s house was Eddie, which was expected of him, his mom, while not exactly wanting him to go (even if she did think Stan’s parents were home), wanted him to arrive early, he also brought snacks, the plan was to just do whatever Bill wanted, as long as it wasn’t search for his brother, though they didn’t think that would come up when it was supposed to be a sleepover. Surprisingly the next to arrive was Richie, who immediately pulled Eddie into a hug and messed with his hair, the shorter boy giving him a death-stare in response. It didn’t take much longer for Bill to arrive on Silver, leaving her around back.

“So what do you want to do Bill?” Stan asked Bill, who was not expecting that, since it was Stan who proposed it and it was at his house.

“Uhh… how about a movie” Bill wanted to do something else, but was too scared to say that at the moment, he recently had been curious about what it would be like to give someone a blowjob, and he did have a crush on all three of his friends, maybe later he thought.

The movie Bill decided on had been some random comedy, he thought it would help distract him from his brother. And it was actually pretty funny, all four boys laughing at different parts of the movie. Bill throughout the movie had shifted closer and closer to Stan, and by the end he was right next to him. He was able to smell the exact shampoo Stan used, which he really liked. Eddie was below him, his head occasionally brushing against his thigh, and Richie was on the other side of Bill. Bill loved that he was surrounded by his friends, it had been a while since the last time something like this had happened and he missed it. After the movie he was asked what he wanted to do know.

“A-Again, are you sure you do-don’t want anyone else to decide?”

“Yeah, we talked about this before. This is to help you feel better Bill. We’ll do anything” 

“Ah-Anything?”

“Yeah” All three of them said, in almost perfect unison, causing Bill to blush some at the thought he had. Might as well ask.

“C-can I umm, can I bl-blow one of you?” As Bill said that he blushed even more, but to his surprise all three of them said yes. Now the hard part, well aside from his dick which was already hard thinking about blowing one of them, deciding which one to blow. 

“Which one of us do you fancy Bill” Richie asked, making a gesture to his crotch.

“A-all of you”

At this point all of them were blushing, Bill had decided to have them all strip and blow the smallest one, after all this would be his first time, might as well go with the smallest one. What he was not expecting was that all were decently big, if he had to guess Richie was the smallest at around 6.2 inches, then Stan who was 6.5 inches, but also the thickest at around 2.8 inches thick, and Eddie surprisingly was 6.8 inches. 

“Wow…” was all Bill could say, he was also decently sized, but he was not expecting this, he was definitely happy but this was amazing. 

Bill moved to sit in front of Richie before slowly moving his head forward down onto his dick. Bill took the tip of Richie’s dick into his mouth, swirling his tongue around it some, before getting slightly more of it into his mouth. Richie’s hands moved to Bill’s short hair, grabbing onto it as he let out a low moan that spurred Bill on even more, he knew he had practically no gag reflex from before so he wasn’t really concerned about that. He hadn’t quite practiced any, just one time accidentally got a lot of banana in his mouth due to Henry one time. After a few minutes Bill had gotten all of Richie into his mouth, careful to not use his teeth, and breathed in some, a scent that was definitely Richie, before pulling back and going back down slowly, both Eddie and Stan watched on, both fully hard. This continued for a few minutes until Richie said something.

“Fuck Bill, you’re better than Mrs. K” As soon as Richie said that, he pulled completely off of Richie’s dick.

“Eddie. Shut him up, you know how, and Stan, c-can you fuh-finger me?” Bill said before going back to blowing Richie.

And Eddie did know how, he walked forward to Richie’s mouth before thrusting his cock into Richie’s already open mouth. And Stan was a little surprised to hear that, but did as Bill asked, putting his fingers in his mouth to get them wet before inserting one into Bill’s ass. Eddie was making sure to not hurt Richie… too much, this was kind of a punishment so he was thrusting pretty fast, making Richie gag some, but less then expected. Bill also sped up on blowing Richie, and Richie was helping with that as well, pulling Bill’s hair and thrusting his hips up. Stan after a few minutes put a second finger into Bill’s tight hole, before scissoring him, opening him up even more, Bill moaning around Richie’s dick, and it wasn’t much longer until Stan put two more fingers into Bill, who on instinct thrusted his ass back against Stan’s fingers. 

“Wow Bill, guess you’re a slut. Already taking four fingers and blowing Richie like a champ apparently” As Stan said this, he used his other hand to slap Bill’s ass, causing him to moan around Richie’s dick again, which caused Richie to cum down Bill’s throat, Bill did his best to swallow it all but some leaked out around his mouth. Richie then pulled out as Eddie did as well, and Stan stopped fingering him to see what he wanted to do now.

“Stan can you… can you fuck me please?” 

It didn’t take long until Stan followed Bill’s question by ramming his thick cock deep into Bill’s ass, both boys moaning. Stan started fucking Bill at a rough pace, causing the couch Bill was leaning against to slide forward with each thrust. Bill loved the new feeling, it barely hurt because of how well Stan prepared him earlier, but… he wanted even more. 

“Eh-Eddie fuck me too!” 

“Are you sure Bill?” As soon as Eddie asked that Bill nodded yes, Stan adjusted how he was fucking Bill some to allow Eddie access Bill’s ass as well.

As soon as Eddie thrust into Bill he whimpered some, causing both Eddie and Stan to stop to make sure he was okay. They allowed Bill a few minutes to get adjusted, until he nodded signaling he was ready for them to fuck him. At first their thrusts were disconnected, but soon enough they were in sync, pounding Bill’s ass hard, almost always hitting his prostate and Bill letting out constant high pitched moans, both Stan and Eddie occasionally letting out grunts or low moans. It didn’t take long for Bill to cum, his cum spraying against the carpet, Bill still begging for more while that was happening. 

“Bill you really are a slut, I wonder how many times we will get you to cum tonight?” Stan said as he continued fucking him with Eddie, Bill moaning when he heard that, he wondered that too, especially with what he was thinking.

“C-Can you two stop for a little bit. I want to t-try something.” Both Eddie and Stan stopping, but not pulling out as Bill seemed to want them to still be inside of him. 

“R-Richie.. finger me as well” Richie obeyed Bill, inserting two of his fingers alongside of Stan and Eddie’s dicks. 

“F-fuck it feels so good” Bill moaned, moving his hips some. Bill then consistently did that as Richie began scissoring him open even more. It wasn’t long until Richie inserted a third finger, Bill moaning again. After thirty minutes of that Bill told Richie to stop, and to see if he could be triple penetrated now. With some maneuvering all boys got into a comfortable position as they tried that, Richie slowly pushing the tip of his dick into Bill’s ass. 

“This feels so amazing” As soon as Bill said that Richie got the rest of his dick into Bill’s ass. 

After a few minutes Bill gave them the okay to start fucking him. And they did, really hard. All three boys doing their best to fuck Bill as fast and hard as they could. Bill came for a second time soon after they started fucking him, his ass clenching hard around the three dicks in his ass. And it didn’t take much longer for the other boys to all cum at the same time, all moaning. Their cum flooding Bill’s ass as he started riding them as their thrusts slowed down. Once they recovered they started fucking Bill again, who was still riding them, his prostate getting repeatedly pounded. All four boys were moaning loudly, sweat clinging to their skin as Bill came to his third orgasm of the night. 

“Please, want more” Bill moaned, and they obliged, fucking him harder. Bill’s moans became intangible mixings of more, faster, harder, and just noises.

Eddie was the next to cum again, with a loud moan, as soon as he came off his high he decided to pull out, making Bill whine some but he understood why Eddie stopped. To everyone surprise after that Bill came once more, a small amount of cum leaking out of his dick, and Richie came soon after, like Eddie pulling out, leaving Stan fucking Bill. Stan moved his head to Bill’s neck and started kissing and leaving hickies there. After a few minutes Bill and Stan came at the same time, Bill’s entire body shaking, no cum coming out of his dick, and Stan still thrusting some until he pulled out, leaving Bill’s ass leaking copious amounts of cum as they all passed out in a sweaty pile as Bill quietly muttered a thank you.


End file.
